“There’s a question I get asked a lot,” Jimmy Kimmel said at the beginning of a recent monologue. “Now that we have this president, people ask, ‘Is it easy now? It must be easy to write jokes, there’s so much material, the jokes must write themselves.’ And it’s not true. We still write the jokes ourselves. And in fact, in a way, it makes it harder to be funny when nonsense and stupidity is pouring on your head at all times.”
Kimmel’s comments were merely a set-up to explain that his jokes didn’t write themselves “until today, when Kanye West visited the White House.” But aside from those rare instances, his sentiment echoes what several late-night hosts have expressed during the first two years of the Trump presidency.
And especially in 2018, it seemed, the late-night men and still-too-few women frequently struggled to find the best ways to joke about this president and the madness that surrounds him. The daily onslaught of crazy from the White House, combined with a viewing public increasingly eager to call out any perceived transgression on social media, led to an unprecedented level of outrage, often of the “faux” variety.
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Here, in chronological order, are the most controversial late-night clips of 2018.
John Oliver’s Trolls Mike Pence with Marlon Bundo Book
The day before Charlotte Pence released her children’s book about a “day in the life” of her father, Vice President Mike Pence, Last Week Tonight host John Oliver published his own, far more successful, parody version. As Oliver explained on his show in March, A Day in the Life of Marlon Bundo tells the story of a gay bunny who wants to get married but is initially thwarted by an evil stink bug who bears a striking resemblance to the vice president.
For her part, Charlotte Pence was surprisingly cool with the rival book, the proceeds from which went to support LGBTQ charities. “I mean, I think, you know, imitation is the most sincere form of flattery in a way,” she said on Fox Business Network. “But also, in all seriousness, his book is contributing to charities that I think we can all get behind. We have two books giving to charities that are about bunnies so I’m all for it really.”
Samantha Bee Calls Ivanka Trump a ‘Feckless Cunt’
As the first writer to cover the joke that almost ended Samantha Bee’s career, I knew it was going to be a thing. During the first in-depth late-night segment on the Trump administration’s new policy of separating migrant families at the U.S.-Mexico border, the Full Frontal host highlighted a recent social-media post from Ivanka Trump in which she was cuddling her son.
“Ivanka Trump, who works at the White House, chose to post the second most oblivious tweet we’ve seen this week,” Bee said, referencing Roseanne Barr’s even more controversial tweet. “You know, Ivanka, that’s a beautiful photo of you and your child, but let me just say, one mother to another, do something about your dad’s immigration practices, you feckless cunt!”
After both White House Press Secretary Sarah Huckabee Sanders and then President Trump himself called for her firing, Bee issued a “sincere” apology and addressed the moment on her next show, acknowledging that she “crossed a line.”
But when I spoke to Bee about the incident this past August, her only real regret was that the line overshadowed the larger point she was trying to make about the kids being held in cages. “A lot of the loudest voices that came out to speak about me should be embarrassed by their own conduct these days,” she said. “I could not give a single fuck what they think of me. And why should I?”
Bill Maher Calls for a Recession to Take Down Trump
Bill Maher didn’t do anything to rival last year’s casual use of the “N-word” in 2018, but there was still plenty for his critics on both sides of the political aisle to complain about. There was his continued insistence on hosting odious right-wing figures like NRATV host Colin Noir, Ben Shapiro and Steve Bannon without forcefully holding them to account—or his deeply problematic takes on the #MeToo movement with frequent guest Bari Weiss. But the moment that caused the biggest uproar was when he called for a recession to hurt Trump.
“I feel like the bottom has to fall out at some point—and by the way, I’m hoping for it, because I think one way you get rid of Trump is a crashing economy,” Bill Maher said in June. “So please, bring on the recession. Sorry if that hurts people, but it’s either root for a recession or you lose your democracy.” The right was not amused.
Two weeks later, Maher put a handful of headlines about those remarks—including one from The Daily Beast—on his screen and declared, “Anyone who went apeshit for the last two weeks because I said going through a recession would be worth it if it undermined Trump’s popularity has to enroll in college and take a course in perspective.”
Jimmy Fallon Gets Sucked Into Trump Feud
Typically the least controversial late-night host, Jimmy Fallon got inadvertently sucked back into a feud with the president this year after he gave an interview to The Hollywood Reporter in which he discussed the fallout from his hair-ruffling, pre-2016 election sit-down with Donald Trump. After Fallon called the entire incident a “mistake” that left him “depressed,” Trump tweeted at him to “be a man.”
That led to a rare rebuke of Trump from Fallon, who joked on The Tonight Show, “Melania, if you’re watching, I don’t think your anti-bullying campaign is working.” After Trump continued to attack him, along with his competitors Jimmy Kimmel and “the guy from CBS,” at a campaign rally, Fallon teamed up with Stephen Colbert to fire back at the president.
Michelle Wolf Turns ICE Into ISIS
With her uncompromising jokes about Sarah Huckabee Sanders at this past year’s White House Correspondents’ Dinner, Michelle Wolf managed to terrify the current Washington establishment before her Netflix show even premiered. She didn’t stop there. During The Break’s too brief three-month run, Wolf compared Ivanka Trump to herpes and led a full-on marching band to declare “God bless abortions!” But it was a sketch in which she portrayed Homeland Security Secretary Kirstjen Nielsen that really got under the right’s skin.
“It’s popular nowadays to say ICE is bad,” Wolf, as Nielsen, said in the sketch. “But there’s no better representation of American values right now than ICE is.” From there, the Immigration and Customs Enforcement officers gradually morphed into Islamic extremists. “Take it from me, no organization is better than ISIS,” she concluded, raising her automatic rifle in the air.
The next day on Fox & Friends, noted humor expert Mike Huckabee said, “I love satire, it’s one of my favorite forms of comedy, but her form of comedy is not satire, it’s angry, bitter hate.”
Stephen Colbert Takes on His CBS Boss Les Moonves
The Late Show host could have waited for his boss to be fired to take him to task over the raft of sexual harassment and assault allegations that came his way this past summer. But he didn’t.
In July, following The New Yorker’s damning exposé about powerful CBS CEO Les Moonves, Stephen Colbert took several minutes to speak frankly and seriously about his boss’ alleged behavior. “I don’t know what’s going to happen, but I do believe in accountability, and not just for politicians you disagree with,” Colbert told his viewers. “Everybody believes in accountability until it’s their guy, and, make no mistake, Les Moonves is my guy.”
The host went on to acknowledge that Moonves had stood by him when people were calling for him to be fired in 2017 for making what some perceived to be a homophobic joke about Trump and Putin. “But accountability is meaningless unless it’s for everybody,” he said, “whether it’s for the leader of a network or the leader of the free world.”
Jimmy Kimmel Leaves Kanye West Speechless
At the height of Kanye West’s odd love affair with Donald Trump, Jimmy Kimmel asked him the one question on everyone’s minds: “I mean, you so famously and so powerfully said, ‘George Bush doesn’t care about black people.’ It makes me wonder what makes you think that Donald Trump does, or any people at all?”
The question left West speechless for several seconds before Kimmel ultimately cut to commercial in what appeared to be an act of generosity. The rapper didn’t take it that way, blasting critics on Twitter, claiming, “I wasn’t stumped. I wasn’t given a chance to answer the question.” Yet he did not take that opportunity to share an answer.
When I spoke to Kimmel in his office a couple of weeks later, the host told me he “felt that his silence answered the question in some ways,” and hoped that he would answer it at some point. Later that month, West finally did try to answer the question during an interview with a Chicago radio station.
“I feel that [Trump] cares about the way black people feel about him, and he would like for black people to like him like they did when he was cool in the rap songs and all this,” West said.
Pete Davidson vs. Lt. Commander Dan Crenshaw on SNL
2018 was not an easy year to be Pete Davidson. The 25-year-old Saturday Night Live cast member, who has always been open about his struggles with mental illness, got engaged to pop singer Ariana Grande only to have the two split just a few months later. He ended the year with a cry for help on Instagram and a brief appearance on SNL’s pre-Christmas show just to let fans know he was still OK.
Between those two personal events, Davidson managed to deliver both the most divisive and most inclusive moments of SNL’s 44th season. First came his pre-midterms joke about now GOP Rep.-Elect Dan Crenshaw, who lost an eye in combat as a Navy SEAL. Davidson said he was “surprised” Crenshaw was a congressional candidate from Texas and “not a hitman in a porno movie,” a line that led the Texas Republican to condemn him on Twitter and Fox News. Even Davidson’s SNL colleague Kenan Thompson said he “crossed the line.”
But then, amidst the outrage, something truly remarkable happened. On the following week’s show, after he won his election to the House, Crenshaw showed up on SNL’s “Weekend Update” to accept Davidson’s face-to-face apology and roast him right back. “He looks like if the meth from Breaking Bad was a person,” Crenshaw said of Davidson. “He looks like a troll doll with a tapeworm.” And then, “He looks like Martin Short in The Santa Clause 3. By the way, one of these people was actually good on SNL.”
With a Little Help From My Friends
And finally, just for fun, here’s the least-controversial, most-beloved late-night clip of 2018: James Corden’s “Carpool Karaoke” with Sir Paul McCartney.
